JPH0527616B2 - - Google Patents
Info
- Publication number
- JPH0527616B2 JPH0527616B2 JP59087964A JP8796484A JPH0527616B2 JP H0527616 B2 JPH0527616 B2 JP H0527616B2 JP 59087964 A JP59087964 A JP 59087964A JP 8796484 A JP8796484 A JP 8796484A JP H0527616 B2 JPH0527616 B2 JP H0527616B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- dimethylamino
- formula
- acid addition
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- JGVZJRHAZOBPMW-UHFFFAOYSA-N 1,3-bis(dimethylamino)propan-2-ol Chemical compound CN(C)CC(O)CN(C)C JGVZJRHAZOBPMW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 230000008569 process Effects 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- -1 2-propyl-4-chlorophenoxy acetate Chemical compound 0.000 claims description 7
- YXUURMMMLNKQFH-UHFFFAOYSA-N [4-chloro-1,5-bis(dimethylamino)-6-propylcyclohexa-2,4-dien-1-yl] ethaneperoxoate Chemical compound C(C)(=O)OOC1(C(C(=C(C=C1)Cl)N(C)C)CCC)N(C)C YXUURMMMLNKQFH-UHFFFAOYSA-N 0.000 claims description 5
- VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 230000003925 brain function Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 1
- RTHMFWSTLJGBPA-UHFFFAOYSA-N 2-[4-chloro-1,5-bis(dimethylamino)-6-propylcyclohexa-2,4-dien-1-yl]oxyacetic acid Chemical compound CCCC1C(N(C)C)=C(Cl)C=CC1(OCC(O)=O)N(C)C RTHMFWSTLJGBPA-UHFFFAOYSA-N 0.000 abstract description 4
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 abstract description 3
- 210000004958 brain cell Anatomy 0.000 abstract description 3
- 230000003340 mental effect Effects 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- XZTYGFHCIAKPGJ-UHFFFAOYSA-N Meclofenoxate Chemical compound CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1 XZTYGFHCIAKPGJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000032677 cell aging Effects 0.000 description 2
- 210000003710 cerebral cortex Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- FBZWYFBNIGSUPS-UHFFFAOYSA-N (2-chlorophenyl) ethaneperoxoate Chemical compound CC(=O)OOC1=CC=CC=C1Cl FBZWYFBNIGSUPS-UHFFFAOYSA-N 0.000 description 1
- OMVLZBRPTYNASP-UHFFFAOYSA-N 1,1-bis(dimethylamino)ethanol Chemical compound CN(C)C(C)(O)N(C)C OMVLZBRPTYNASP-UHFFFAOYSA-N 0.000 description 1
- BOBLSBAZCVBABY-WPWUJOAOSA-N 1,6-diphenylhexatriene Chemical compound C=1C=CC=CC=1\C=C\C=C\C=C\C1=CC=CC=C1 BOBLSBAZCVBABY-WPWUJOAOSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YUGDKEWUYZXXRU-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetonitrile Chemical compound ClC1=CC=C(OCC#N)C=C1 YUGDKEWUYZXXRU-UHFFFAOYSA-N 0.000 description 1
- FSHOYFLJXMSRNC-UHFFFAOYSA-N 2-chloro-n,n,n',n'-tetraethylpropane-1,3-diamine Chemical compound CCN(CC)CC(Cl)CN(CC)CC FSHOYFLJXMSRNC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KXXFHARWKGDIMP-UHFFFAOYSA-N [2-(4-chlorophenoxy)acetyl] 2-(4-chlorophenoxy)acetate Chemical compound C1=CC(Cl)=CC=C1OCC(=O)OC(=O)COC1=CC=C(Cl)C=C1 KXXFHARWKGDIMP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000004098 cellular respiration Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- FVRABHGHBLRNNR-UHFFFAOYSA-N liriodenine Natural products O=C1C=CC=c2c1cc3nccc4cc5OCOc5c2c34 FVRABHGHBLRNNR-UHFFFAOYSA-N 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- OSGZHKYFZSNKRI-UHFFFAOYSA-N methyl 2-(4-chlorophenoxy)acetate Chemical compound COC(=O)COC1=CC=C(Cl)C=C1 OSGZHKYFZSNKRI-UHFFFAOYSA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- CETFXLWWGIUWAI-UHFFFAOYSA-M sodium;2-(4-chlorophenoxy)acetate Chemical compound [Na+].[O-]C(=O)COC1=CC=C(Cl)C=C1 CETFXLWWGIUWAI-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/20—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C219/22—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Detergent Compositions (AREA)
- Devices For Use In Laboratory Experiments (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU2251-1496/83 | 1983-05-02 | ||
| HU831496A HU190589B (en) | 1983-05-02 | 1983-05-02 | Process for preparing acid additional salts of 4-chloro-phenoxy-acetic acid-1,3-bis/dimethyl-amino/-2-propyl-ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS606646A JPS606646A (ja) | 1985-01-14 |
| JPH0527616B2 true JPH0527616B2 (cs) | 1993-04-21 |
Family
ID=10954727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59087964A Granted JPS606646A (ja) | 1983-05-02 | 1984-05-02 | １，３−ビス（ジメチルアミノ）−２−プロピル−４−クロロフエノキシアセテ−ト，その製法及び医薬組成物 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4661618A (cs) |
| EP (1) | EP0127000B1 (cs) |
| JP (1) | JPS606646A (cs) |
| KR (1) | KR840009292A (cs) |
| AT (1) | ATE24712T1 (cs) |
| AU (1) | AU565723B2 (cs) |
| BG (1) | BG42833A3 (cs) |
| CA (1) | CA1246602A (cs) |
| CS (1) | CS241081B2 (cs) |
| DD (1) | DD216449A5 (cs) |
| DE (1) | DE3461924D1 (cs) |
| DK (1) | DK214884A (cs) |
| EG (1) | EG16744A (cs) |
| ES (1) | ES8506259A1 (cs) |
| FI (1) | FI81562C (cs) |
| HU (1) | HU190589B (cs) |
| IL (1) | IL71714A (cs) |
| NZ (1) | NZ208011A (cs) |
| PL (1) | PL142906B1 (cs) |
| SU (2) | SU1376937A3 (cs) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3546273A (en) * | 1967-06-01 | 1970-12-08 | Merck & Co Inc | Ester derivatives of 2-(4-halophenoxy)alkanoic acids |
| JPS5135896B2 (cs) * | 1973-06-20 | 1976-10-05 |
-
1983
- 1983-05-02 HU HU831496A patent/HU190589B/hu unknown
-
1984
- 1984-04-03 EG EG271/84A patent/EG16744A/xx active
- 1984-04-24 FI FI841611A patent/FI81562C/fi not_active IP Right Cessation
- 1984-04-26 CA CA000452851A patent/CA1246602A/en not_active Expired
- 1984-04-27 DK DK214884A patent/DK214884A/da not_active Application Discontinuation
- 1984-04-27 BG BG8465259A patent/BG42833A3/xx unknown
- 1984-04-27 SU SU843732702A patent/SU1376937A3/ru active
- 1984-04-28 CS CS843217A patent/CS241081B2/cs unknown
- 1984-04-30 DD DD84262463A patent/DD216449A5/de not_active IP Right Cessation
- 1984-04-30 ES ES532062A patent/ES8506259A1/es not_active Expired
- 1984-05-01 NZ NZ208011A patent/NZ208011A/en unknown
- 1984-05-01 IL IL71714A patent/IL71714A/xx unknown
- 1984-05-02 DE DE8484104880T patent/DE3461924D1/de not_active Expired
- 1984-05-02 EP EP84104880A patent/EP0127000B1/de not_active Expired
- 1984-05-02 AT AT84104880T patent/ATE24712T1/de not_active IP Right Cessation
- 1984-05-02 PL PL1984247504A patent/PL142906B1/pl unknown
- 1984-05-02 KR KR1019840002367A patent/KR840009292A/ko not_active Application Discontinuation
- 1984-05-02 US US06/606,347 patent/US4661618A/en not_active Expired - Fee Related
- 1984-05-02 JP JP59087964A patent/JPS606646A/ja active Granted
- 1984-05-02 AU AU27610/84A patent/AU565723B2/en not_active Ceased
-
1985
- 1985-07-02 SU SU853915275A patent/SU1326572A1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| PL247504A1 (en) | 1985-03-26 |
| EG16744A (en) | 1990-12-30 |
| EP0127000B1 (de) | 1987-01-07 |
| ES532062A0 (es) | 1985-07-01 |
| CS321784A2 (en) | 1985-06-13 |
| ATE24712T1 (de) | 1987-01-15 |
| DK214884D0 (da) | 1984-04-27 |
| AU565723B2 (en) | 1987-09-24 |
| NZ208011A (en) | 1987-06-30 |
| CS241081B2 (en) | 1986-03-13 |
| FI841611A0 (fi) | 1984-04-24 |
| KR840009292A (ko) | 1984-12-26 |
| FI841611A (fi) | 1984-11-03 |
| PL142906B1 (en) | 1987-12-31 |
| DK214884A (da) | 1984-11-03 |
| HUT34150A (en) | 1985-02-28 |
| US4661618A (en) | 1987-04-28 |
| SU1326572A1 (ru) | 1987-07-30 |
| CA1246602A (en) | 1988-12-13 |
| DD216449A5 (de) | 1984-12-12 |
| FI81562B (fi) | 1990-07-31 |
| ES8506259A1 (es) | 1985-07-01 |
| IL71714A (en) | 1987-09-16 |
| JPS606646A (ja) | 1985-01-14 |
| DE3461924D1 (en) | 1987-02-12 |
| BG42833A3 (en) | 1988-02-15 |
| EP0127000A1 (de) | 1984-12-05 |
| AU2761084A (en) | 1984-11-08 |
| IL71714A0 (en) | 1984-09-30 |
| SU1376937A3 (ru) | 1988-02-23 |
| FI81562C (fi) | 1990-11-12 |
| HU190589B (en) | 1986-09-29 |
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